What Might Have Been
by Slovesemmett
Summary: Post Season Seven - Rory ponders what might have been from the campaign trail. Mainly where she would be now had any of her previous significant relationships had stuck.
1. Prologue

**What Might Have Been**

**Set: Post Season 7**

* * *

Rory Gilmore leaned her head against the window of the bus and watched the scenery fly by. She'd been on the campaign trail for a month, and she'd learned a few things. First, some reporters would do anything for a scoop. Second, she HATED traveling by bus. And third, she had way too much time on her hands.

The song changed on her iPod and she closed her eyes having seen enough cornfields to last a lifetime.

_Sure I think about you now and then_

_But it's been a long long time_

_I've got a good life now I've moved on_

_So when you cross my mind_

_I try not to think about_

_What might have been_

_'Cause that was then_

_And we have taken different roads_

_We can't go back again_

_There's no use giving in_

_And there's no way to know_

_What might have been_

The song filtered into her brain as she began to hum along. She hadn't heard it in years, her mother must have some how slipped it into her playlist and it just hadn't come up before now.

As a general rule, she tried very hard not to think about the past, there was no use in it. It was not like she could go back and change anything, but now, with all this time for reflection, she couldn't help but wonder… What Might Have Been.

* * *

**Okay I know I have two stories going already, but I heard this song the other day, and I can't get it off my mind. So here's the plan… this is a short story, about where Rory would be instead of sitting on the bus following the campaign had she stayed with any of the significant men in her life. There are some people that will get two chapters based on break ups and being different the second time around. They will go chronologically in the following order:**

**Dean I**

**Tristan**

**Jess I**

**Dean II**

**Marty**

**Logan I**

**Jess II**

**Logan II**

**The chapters in this will be much shorter than Winning Back the Gilmore Girls, probably along the length of the chapters in Blood Is Thicker Than Water or Stars Hollow On Shuffle. **

**So what do you think? Like it? Hate it?**

**Oh and the song is What Might Have Been by Little Texas.**

**And thanks to DramaQueen1103 - again, for reading this ahead of time, and encouraging me to post it.**

**S**


	2. Dean I

Rory Forrester looked into the mirror and smoothed the sundress over her 20-week pregnant belly. She smiled as she affectionately rubbed the bump.

"Rory, hurry up! My mom is expecting us for dinner in ten minutes," Dean called to her.

"Dean they live five minutes away. On foot even. We're fine!" she called back. She rolled her eyes, and smiled again. "I'm almost ready, I just have to find my shoes."

"Sorry, I know. My mom is just really excited, she's already called me half a dozen times today, trying to get me to tell her what we're having."

"You didn't tell her, did you?" Rory asked suddenly filled with horror, if Dean's mom found out before her mom did, there would be hell to pay.

"Of course not. I told her she'd find out tonight, at dinner, at the exact same time as Luke and Lorelai found out."

"Thank you!" she said, feeling very relieved. Dean came into their bedroom and sat down on the queen-sized bed. "You know, watching me won't make me get ready any faster."

"I know, but I like to watch you get ready. You're cute Mrs. Forrester," he said with a flirtatious smile.

"Thank you Mr. Forrester," she replied, turning to kiss him sweetly on the cheek. "Do you know where my white sandals are?"

"I think they're in the hall closet," he told her.

"You're right!"

"Does this mean you're ready to go?"

"Yes, I'm ready to go." She exited the bedroom and headed down the hall to the foyer and the hall closet.

She picked up her purse from the side table, and opened the closet to find her shoes. The closet was filled with shoes, and coats, and the vacuum cleaner. She dug around for a minute and finally pulled out one of the shoes she was looking for. "Here, hold this!" she said thrusting the shoe at her husband. "I'm going back in for the other one. If I don't come out in five minutes, send in a search party."

Dean took the shoe and laughed. "You know, this wouldn't be a problem if you didn't have so many shoes."

"Ha!" she snorted from the closet. "You think this is a lot of shoes? Compared to my mom-"

Dean cut her off, "I know your mom has twice this many shoes."

"Exactly!" Rory exclaimed. "And my grandmother has at least twice as many shoes as my mother. You're lucky you got this Gilmore, Buddy."

"Yes, yes I am," he said with a smile.

"Ah-ha!" Rory yelled triumphantly. "I've got you now!" She backed out of the closet holding up the other white sandal. She dropped it on the floor and slid her foot into it, then held out her hand to Dean for the other one. He handed it to her and she dropped it on the floor, and slid into it. "I'm really ready now."

Dean smiled at her, and she walked out the door with him a step behind her, pausing only to lock the door. He grasped her hand, and they walked down the street to his parents' house together.

* * *

"So?" Mae Forrester asked the moment they walked in the door.

"So, what?" Dean teased his mother.

"Is it a boy or a girl?"

"We're not telling you until everyone gets here," Dean reminded her.

"We're here! I hope we didn't miss the big announcement," Lorelai said as she and Luke came in the door behind Rory and Dean.

"Geez Lorelai, you didn't even bother to knock!" Luke scolded her.

"This is my daughter's mother-in-law's house. It's family, there's no need to knock!" Lorelai explained.

"Exactly right!" John Forrester concurred, coming out of his study.

"We're all here, now will you tell us?" Mae asked again.

"Alright, alright," Dean started, "it's a…"

"Girl!" Rory shouted, not being able to stand the suspense of drawing it out.

"I knew it!" Lorelai exclaimed. "Another Lorelai?"

"Congratulations," Mae said excited.

"We haven't picked a name yet," Rory said answering her mother's question. The pair were congratulated by all, and smothered in hugs and kisses.

"So, is dinner soon?" Dean asked.

"Oh yeah, it's ready now, the picnic table is set in the back yard," his mother told them.

"Well let's go eat and we'll discuss the details over dinner," John said, ushering the crowd of people from his entryway into the back yard.

* * *

The table was set with typical summer fare, barbequed chicken, corn on the cob, baked beans, potato salad, fresh fruit and lemonade. The six of them, and Dean's sister Clara, all took their places around the table and began to dig in.

"So Rory, how much longer are you going to keep working?" John asked.

"Well, as a staff writer, I can pretty much keep working until I pop, then work from home while I'm on maternity leave," she explained. Rory had been at the Stars Hollow Gazette since she started college. She'd had a full ride to Connecticut State, and chose to go there and stay close to Dean instead of going to Harvard or Yale. She was hired on full time just a few months earlier when she'd graduated from college.

"Rory, the whole point of maternity leave is that you don't have to work," her mother explained in a joking manner.

"I know, but I like my job, and we need the money."

"Honey, if you don't want to work once the baby is born I can pick up some extra shifts at Doose's," Dean told her.

"No!" she exclaimed louder than she intended to. "With the hours you work for Tom I already hardly ever see you, if you pick up more shifts at Doose's, then I'll never see you." He just nodded at her.

"Well I'll babysit my niece any time you want," Clara informed them happily. "For free even!"

"I can't believe my baby is having a baby!" Lorelai said.

"I'm 22 Mom, not a baby."

"I'm surprised it hasn't happened sooner," Mae said. "I mean they've been married for two years already!"

"Rory wanted to finish college first, Mom," Dean explained.

Rory sighed lightly and tried to refrain from rolling her eyes, leave it to Dean to put their delay in having children all on her shoulders.

"Either way, I'm glad they're having one now! I can't wait to meet my granddaughter," John interjected hoping to stop any potential arguments.

"To Dean and Rory," Luke said, holding up his lemonade glass. "Congratulations on… Baby Girl Forrester," he concluded awkwardly.

"Thank you Luke," Rory told him with a smile.

* * *

Three hours later Rory and Dean exited the elder Forrester's house and headed back towards their apartment. The key stuck in the lock as Dean tried to open the door.

"I really hate this apartment," he said gruffly.

"Well, we should consider moving soon, this place isn't really big enough for us now, and when the baby gets here it'll be even more crowded."

Dean shoved the door roughly and walked into the apartment, sighing deeply as he headed for the living room sofa. He plopped down and rested his elbows on his knees, dropping his head into his hands.

"Are you okay Babe?" Rory asked as she slipped off her shoes and followed him into the living room.

"Yeah," he said with a sigh, "I just feel frustrated. We need a bigger apartment, and you shouldn't have to work after the baby is born. I feel like I can't even take care of my family!"

"Don't say that," Rory said, sitting down beside him. "I like my job, I like to work. Maternity leave would make me stir crazy. And so what if we can't afford a bigger apartment right now. I know this one sucks, but we can make it work for a while longer."

"I'm sorry I can't give you everything," Dean said solemnly. "If you were with one of those rich guys your grandparents approved of you wouldn't have to worry about any of this."

"I don't want those guys, I only want you. Besides, there's no use wondering about What Might Have Been. We're here now, and we're happy, we both have jobs, and we have a healthy baby girl on the way."

"I love you Rory."

"I love you too," she told him. "Now, I'm tired and craving ice cream, why don't you, Ben and Jerry, and I all climb into bed and watch Willy Wonka?"

"Okay," he said standing up from the couch.

"I'm going to grab the ice cream and I'll be right in." He nodded in acknowledgement and headed into the bedroom.

Rory went into their tiny kitchen and pulled out the Chunky Monkey and a couple of spoons, turned out the lights, and headed to bed.

* * *

**AN: I don't own the song or the show. I also don't own Ben and Jerry's. **

**Let me know what you think… Reviews make my day!**

**Next up Tristan!**


	3. Tristan

"Wake up Mar, we're home."

"Huh?" she said sleepily.

"You fell asleep in the car between the airport and the house, and we're here now, so you need to wake up enough to get out of the car. I don't mind if you sleep here, but the driver probably has other people to pick up," Tristan teased as he opened the door of the black town car.

Rory rubbed her eyes and slid across the seat towards the door. Tristan extended his hand to help her out of the car.

The driver stood patiently by the side of the car next to the luggage he had pulled from the trunk. "Do you need help getting the luggage into the house Sir?" he asked kindly.

"That'd be great actually," Tristan told him, giving him a $20 handshake. "Come on Mary," he said as he picked her up and carried her towards the house, leading the way up the path to their brownstone for the driver to follow.

"I'm perfectly capable of walking you know," she mumbled sleepily.

"I know babe, but this is our first entrance into the house as husband and wife, it would be wrong if I didn't carry you over the threshold." He smiled down at her, as she nestled into his chest. When he reached the door, he adjusted his grip on his wife and fumbled around in his pocket for the house keys. He got the door open, and strode purposefully into the foyer while the driver hauled the suitcases in right behind them.

"If that is all sir?" the driver asked, making sure they were done before he left.

"Yes, thank you very much," Tristan told him.

The driver smiled and left the house, heading back to his car, leaving the newlyweds in peace.

* * *

"Come on Mary, let's get you into bed," Tristan said to the woman sleeping in his arms. He started towards the stairs to head up to their bedroom.

"You know, we're married, you know I'm not a Mary, do you think you'll ever let that name drop?" she asked quietly with a yawn.

"Nope. You'll always be my Mary, like it or not."

She was silent as he carried her up the stairs and into their bedroom. He walked over to the bed and dropped her on it, jolting her awake with the bounce.

"What the-" she started.

"I know you're tired, but we can't let our first night in this house as a married could go by uncelebrated."

She opened her eyes and looked around the room. There were rose petals everywhere. She blinked a few times, making sure she wasn't seeing things, then looked up at her husband. "Did you do this?"

"Nope. But I think I know who did."

Rory looked around the room again, looking for clues. Next to the fireplace was a bottle of champagne in a bucket of ice, and a tray of chocolate dipped strawberries, expertly painted with both white and dark chocolate. On the dresser was a thermos full of coffee and a tray of Mallomars.

"My mother was here!" she exclaimed suddenly wide-awake. She ran to retrieve her cell phone from her purse.

"Rory, I bet a call to your mom could wait until tomorrow morning," Tristan told her. "We don't want the champagne to get warm or the coffee to get cold."

It was too late, she was already dialing.

"Loin-fruit!" Lorelai answered on the first ring.

"Mom!"

"How was Barbados?"

"Two weeks of bliss."

"Did you enjoy my surprise?"

"Not yet, we just got home and I had to call to say thank you."

"You called me before you drank champagne, ate Mallomars and took that gorgeous hunk of a husband of yours to bed? Have I taught you nothing?"

"Sorry…" Rory said sheepishly.

"Call me back tomorrow and thank me properly with all the smutty details."

"Mom!" Rory cried blushing furiously.

"Fine, leave out the smutty details, but still, call me tomorrow."

"Okay."

"Love you Sweets."

"Love you too."

"Welcome home." Rory heard the deafening silence of being hung up on.

"I can't believe my mother drove all the way to Boston to do this for us," she said with a smile.

"I can. She loves you."

Rory shrugged and walked over to the fireplace. "Champagne Mr. DuGrey?"

"Of course Mrs. DuGrey," he replied with a smile.

"It's still Gilmore you know," she told him.

"I know, I know. But it's Gilmore for work and DuGrey at home right?" he asked slightly apprehensively.

"Exactly," she told him. "Could you open this champagne? I'll bring the coffee and the Mallomars over."

He took the bottle from her and began to unwind the wire wrapping around the cork. Then he grabbed a towel and quickly popped the cork, managing to retain control of the cork, not spill any of the champagne, and still get the popping sound that Rory loved.

"You're so good at that," she said as she returned with the coffee and cookies.

"Well you can fix coffee in your sleep and I can open champagne bottles in mine," he said with a grin.

He poured two flutes of champagne as she fixed two mugs of coffee. "Don't you think coffee and champagne is an odd combination?" he asked.

"Of course not, coffee goes with everything," she answered as though it was completely obvious.

"Of course," he repeated handing her a glass of the bubbly.

"Shall we toast?"

He thought for a minute, "Well Ms. Boston Globe, you're the writer, you should make the toast."

"I can't believe I start at the Globe on Monday," she squealed slightly. It'd been a month since she'd gotten news of the job, but she still hadn't gotten over the excitement, with graduation, the wedding and the honeymoon they'd delayed her start date, so she'd yet to have a first day.

"You'll do great," Tristan told her. "Now the toast…"

"Oh right. To us. I never thought we'd get here, but I'm so glad we are." She held up her glass, and he clinked his against it.

"To us."

They sipped their champagne and Tristan grabbed the tray of strawberries to offer one to Rory.

"It's fruit," she said wrinkling her nose.

"But it's chocolate covered fruit."

"There's still fruit in the middle, I'd prefer the Mallomars."

"Then why did your mom bring the strawberries?"

"For you of course!"

"That's nice of her," he said as he set the tray down and picked up one of the strawberries. "Wait, are they poisoned?"

"She likes you now!"

"She still calls me Bible Boy," he reminded her.

"You still call me Mary."

"True enough." He popped the strawberry into his mouth. "These really are delicious, are you sure you don't want one?" he asked with his mouth full.

"Maybe," she said hesitantly.

"Well sit down on the floor and let me feed it to you."

"I'm not a child, I can feed myself."

"It's supposed to be romantic," he said with a huff.

"Alright," she said in defeat. She pulled a pillow off the love seat and sat down on the floor in front of the fireplace. Tristan flicked the switch to turn the fire on, and grabbed a berry off the tray sitting down next to Rory on the floor.

"Open your mouth," he whispered in her ear. She obliged and he ran the chocolate dipped berry around her lips before putting the tip of it into her mouth. "Now bite," he instructed. She bit down cracking the chocolate and taking part of it as well as part of the berry into her mouth, chewing carefully as if the fruit were going to injure her.

"Mmmmm," she moaned, "That is good. Your turn!" She took the rest of the berry from his hand and consumed it before reaching up to get a fresh one off the tray for him. She mimicked his motions to feed the berry to him.

"I told you they were good," he said as he swallowed the mouthful she'd fed him.

"You were right," she admitted. "You've got a little chocolate on your lip."

He licked his lips trying to find the offending bit.

"Here, let me get it," she said, leaning in to kiss him.

"You'd think a pair of Harvard grads could manage to eat without getting it everywhere," he said with a laugh.

"You'd think," she repeated in a husky voice, then leaned in the rest of the way and kissed him.

He wrapped his arms around her, keeping her close as kissed her. Her hands traveled down his chest to pull his shirt from his pants, and his own hands slid up the back of her already untucked shirt.

"Bed," she whispered hoarsely.

He disentangled himself from her long enough to stand up and pull her across the room to the bed, flinging back the duvet scattering rose petals everywhere. She giggled and he picked her up and threw her on the bed, diving on the bed right after her himself.

* * *

An hour later she looked over at the sleeping form of her husband and couldn't help but smile. She never imagined that she'd end up here, with him of all people, but now that she was, she couldn't imagine being any happier.

"What are you thinking about?" he said, his voice full of sleep.

"What Might Have Been," she replied.

"And?"

"I've decided it doesn't matter, because I couldn't possibly be any happier than I am right now." She leaned down to kiss him.

"Good answer." He gathered her in his arms and they fell into a deep peaceful sleep.

* * *

**AN: I don't own the show (or the song) or Mallomars. Also – in this Tristan is NOT a Military man – only because I think if he and Rory got together in high school, he wouldn't have messed around with Duncan and Bowman, thus he would have stayed in Hartford.**

**Thanks for reading, please review. **

**Up next – the first appearance of Jess.**

**S**


	4. Jess I

"Gilmore!" her editor shouted.

"Yeah?" she called back across the crowded newsroom.

"Simmons just called in sick, you need to go cover the governor's speech," he barked at her.

"Yes sir, I'm on my way." She grabbed her tape recorder and her notebook and stuffed them in her bag as she headed out of the newsroom, down to her car. She fumbled around in the same bag trying to locate both her keys and her cell phone.

She entered the parking garage and beeped open the doors to her aging Toyota, the one she'd gotten years earlier at her high school graduation. She threw her bag on the passenger's seat and started the car. She scrolled through her contacts list to find Jess's number, and pulled it up, waiting until she exited the garage to hit send.

"Hello?" he answered on the second ring.

"I'm going to be late tonight," she said foregoing a usual greeting.

"What do you have to cover this time?" he asked. "A kindergarten art show? A panda at the zoo giving birth?"

"Ha ha Jess," she said sarcastically. As a rookie she usually did get the 'human interest stuff' like that, so he wasn't being all that obscure. "Actually I'm covering the governator's speech."

"How'd that happen?"

"Simmons called in sick."

"Way to go Rory! Do you have a great question prepared for Arnold?" he asked in a faux Austrian accent.

"No Rainier Wolfcastle, I don't. Any ideas?"

"Something about the legalization of marijuana? Or maybe something on same sex marriage? Those are always hot button items."

"Yeah, but he always gets asked about them," she said wistfully.

"Ask about reviving the economy at Venice Beach," he told her.

"How are your dad and Sasha doing by the way?"

"Actually they're doing pretty well, except they want to go on vacation and think that I should run the stand while they're gone."

"Don't they know that you're busy?" She couldn't believe the nerve of his father. "And that you haven't served a hot dog in 5 years?"

"According to my father serving dogs is like riding a bike, once you learn to do it, you never forget."

"Well what did you tell him?" she asked impatiently, honking her horn at the Lexus that just cut her off.

"I told him I could do it for the weekend, but not during the week."

"Jess," she whined, "the weekends are our only times together, with me working days and you working nights."

"I know, but he's my dad, and I want to help," Jess explained. "Maybe you can come down there on Saturday and sling dogs with me?"

"Maybe."

"Well that's a start I guess. So what time will you be home?"

"Probably late, after you leave for work," she told him sullenly. "So how was school today?"

"Fine. Nothing major happened. It's just a state school Ror, I don't see why you care. It's not like Stanford," he said sharply.

"Hey don't knock my alma mater! And I don't care what school you go to, I'm just proud of you for going."

"Yeah, I know," he paused for a moment then continued, "so, I've got late bar tonight, I probably won't be home until around 3:00."

"I know the drill," she told him with a sigh. "Just kiss me before you go to sleep."

"Good luck on your press conference."

"Thanks Jess. I'll see you… later."

"Bye."

She tossed her phone into the passenger seat and leaned to the side, trying to see what was causing the gridlock, but to no avail. She sighed, cranked up The Killers and tried to think of an intelligent question for Ah-nold.

* * *

It was 10:00 by the time she finally pulled into the parking lot at their apartment building. She hauled her bag off the passenger seat and practically dragged it into the apartment. She unlocked the door, stepped inside and kicked off her shoes. Had she known about the press conference in advance she would have worn flats, or at least lower heels, her feet were killing her.

She flicked on the light and wandered into the kitchen. She noticed Jess's school books scattered across the dining room table, and decided to see what he was up to. After she got a snack. She opened the fridge to find it stocked with healthy ingredients. Luke had rubbed off on Jess, who did most of the cooking, and he mainly cooked healthy food. She pushed past some veggies to grab the carton of Chinese food left over from their dinner two nights before, checking to make sure it was still good before popping it in the microwave. She started the coffee pot while she waited for the food to heat, and soon the kitchen was filled with an interesting aroma that was part coffee part General Tso's Chicken.

She pulled the take out box from the microwave when it dinged, grabbed a fork and headed for the dining room table. She took a seat and a bite of the chicken, and examined the books. There was a calculus book, Plato's Republic, a chemistry textbook, and a well-worn copy of Catcher In The Rye. She instantly grabbed the novel and began to page through it, smiling at Jess's tiny scrawled notes in the margins. She couldn't help herself and she grabbed a pen and began to read as well, making her own notes next to his. The beep of the coffee pot, indicating that the nectar of life was now ready for consumption, brought her back to the present, and she set down the book to go get a cup.

When she retuned to the table she finished off the Chinese food, then dove back into Holden Caufield's world, not to be disturbed until her phone chimed around midnight with a text message from Jess. _Night babe, hope your PC went well. Love you. _ She smiled at the phone and texted him back immediately. _It went fine. Tell you about it tomorrow. Love you. _Noticing the time she put down the novel and went to get ready for bed.

* * *

Jess crept into the apartment around 3:00, trying his best to be silent, not wanting to wake his sleeping girlfriend. He wandered into the kitchen for a snack, and ended up with an apple from the fridge when he found that the Chinese food he wanted was gone.

He sat down at the table to eat while he unwound from his day. He grabbed Catcher In The Rye, a novel he'd read several times before, but was now reading again for his Freshman Lit class, and flipped through it to find his spot. He chuckled aloud as he noticed Rory's neat writing in the margins next to his own. She never could resist homework.

"Jess?" she called from the bedroom. "Is that you?"

"No, it's the boogeyman," he teased. "What are you doing up?"

"I thought I heard laughing, then I saw the light on."

He got up and walked into the bedroom to find her in their bed in one of her Stanford tee shirts, and he knew she was wearing a pair of his boxers under the covers as well.

"I didn't mean to wake you," he said softly, "but your notes in my homework just made me laugh."

"Sorry," she apologized, "I just couldn't resist."

"I know. So how was Arnold?"

"Good," she said through a yawn.

"Did you get to ask a question?"

"Nope. But I had a good one."

"I'm sure you did. Why don't you go back to sleep babe?"

"Okay. Are you coming to bed soon?"

"I'll be in in a few," he assured her. She closed her eyes and he kissed her forehead.

"Love you," she murmured.

"Love you too." He started to walk out the door then stopped. "Hey Ror?"

"Yah?"

"Are you happy here?"

"Mmm-hmmm why?"

"Just checking. I mean Stanford and the LA Times were never on your list."

"Things change. They are what they are, we can't go back and change them now."

"But would you want to?"

She sat up in bed and brushed her hair back out of her face. "What's with the What Might Have Been bit tonight Jess?"

"I don't know. Your notes in my book just got me thinking. How could a girl like you end up with a guy like me, who's just now getting around to getting a college education?"

"Love works in mysterious ways," she told him simply. "Besides, if not for you, who else would I have great book debates with? Now can I go back to sleep?"

He smiled at her. "Yeah, sorry about waking you."

"Come to bed soon," she called after him.

* * *

**AN: I still don't own the show or the song. I also don't own any of the books Jess was using for school. Okay fine, I might have a copy of Catcher in the Rye lying around, but that's it. **

**Please read and review – I know for the most part these are pretty happy pieces, but I hope you like them anyhow. (With such short snips – basically a day in the life I don't really feel the urge to go into the trials and tribulations of each relationship). **

**Anyhow – all feedback is welcome.**

**S**


	5. Dean II

She sat at her desk, pencil in her mouth, staring at the screen in front of her, willing the article she was working on to take form. The sound of a throat being cleared made her look up from her monitor.

She looked up to find her boyfriend standing over her with a cup of coffee in his hand. "Dean, what are you doing here?" she asked after she removed the pencil from her mouth.

"Well, it's 7:00 at night and I haven't been able to get a hold of you. I tried your mom but she had no idea where you were, so I thought I'd check your office at the paper," he said trying to keep the irritation from his voice.

"I'm sorry," she started as she reached over on her desk and retrieved her cell phone. She looked down at the screen to see 15 missed calls; he really had been trying to get a hold of her for a while. "It's on silent."

"It's two feet away from you Rory, how could you not hear the vibrations?" Dean asked incredulously.

"I turned the vibration off, it was too loud and distracting in interviews," she explained.

"So how much longer do you have here? Can we go out to dinner?"

She looked across the piles of paper strewn around her desk, and at the partially completed article in front of her and tried to calculate how long it would take to finish. "I think I can get a first draft of this article finished in 30 minutes, then we can have dinner."

"Okay."

She bent her head and went back to focusing on her work, but a moment later she could tell Dean was still standing over her, watching. "I can't work with you staring at me," she told him.

"Where am I supposed to go?"

She thought about it for a moment, "there's a couch in the break room down the hall, go there. There's magazines and such on the coffee table."

"Alright. Which way?" he asked to confirm.

She stood up and pointed down the hall, "first door on the left." She watched as he loped down the hall, and tried to quickly refocus her brain on her work.

* * *

Twenty-nine minutes, and thirty seconds later, she heard heavy footsteps heading her way.

"Are you ready to go?" Dean asked.

"Yep… I'm…" she paused in her speaking to type a sentence.

"Rory!"

"…done." She saved the file she was working on, and emailed it to herself so she could edit it from home. "Let's go."

She shut off her computer, grabbed her purse and headed for the door.

They exited the building on to a busy street in Hartford, and she enjoyed the warmth of the late evening summer heat. "So where do you want to go for dinner?" she asked.

"I don't care, what ever you want is fine," he answered.

"There's a great Thai place at the end of the block," she suggested. She looked up at him to find him making a face, pinched with discomfort. "Okay, then how about Indian food?" He furrowed his brow and shook his head. "Okay then Dean why don't you tell me where YOU want to go," she said getting annoyed.

"Anywhere is fine," he reiterated.

"Obviously _anywhere _is NOT fine. Everywhere I've suggested has been met with a look of disgust."

"Rory, I…"

"You know what, why don't you just tell me what kind of food you want, and I'll suggest a place based on that," she said trying to calm her temper.

"Okay, that's a good idea. I'm really craving a burger," he confessed.

"No good. No place compares to Luke's and we really don't want to drive 30 minutes for dinner. Next?"

"Wanna share a pizza?" he asked.

She thought about it for a moment, knowing she wasn't likely to get a better compromise out of him. "Yeah that's good. Geno's on the next block is really good."

"Well lead the way."

* * *

He opened the door of Geno's Pizza for her, and she stepped into the crowded restaurant.

"Hey Rory!" one of the guys behind the bar called. "How are you?"

"I'm good Sam," she called back with a smile.

"Table for two tonight, or are you going to eat at the bar?"

"Table would be good," she told him.

"Take a seat anywhere and I'll send Maria over in a second to take your order. I'll put the breadsticks on now." He grinned at her.

"Thanks Sam!"

"Do you come here often?" Dean asked curiously as she lead them to a table in the corner.

"A couple times a week for lunch," she said with a shrug.

"Well Sam certainly seems to know you."

"He's a bartender slash waiter. It's his job to remember customers, it helps him earn bigger tips," she said annoyed at his implication.

"Well you must be a big tipper because he even knew what you wanted to start with," Dean said jealously.

"I don't tip Sam with money, I just give him low grade sexual favors in return for good service," she spat sarcastically.

"Rory!" Dean exclaimed.

"What? That's what you're treating this like! I come here a couple times a week for lunch, Sam always has the lunch shift. We always start with breadsticks, and I usually have to order more because I eat most of them myself. There's nothing sinister going on!" she told him exasperatedly. "Honestly I'm not sure what more you want from me. I've never cheated on you. Do you want a contract signed in blood saying that I never will?"

"No," he said quietly. "I just feel like I never see you. And it bothers me that other random people know more about your life than I do."

"We live together Dean, you've seen me more in the month since graduation than you did during my entire senior year at Yale."

"I know. But it just feels like you're never home."

"Well the feeling is mutual buster," she said with a smile. "I can't remember the last time I woke up in the morning and you were still in bed next to me."

"You know that we start early to beat the heat," he said immediately defensive.

"I know that. I'm just saying that you're not the only one that feels like they don't get to see their significant other."

"I guess."

"Hey Rory, do you guys want a couple of beers?" Maria asked as she stopped by the table with the menus.

"Sure, let's just get a pitcher of whatever's light on tap. Is that okay with you?" she asked Dean.

"Sounds fine."

"Do you know what you want already or do you need time to decide?" Maria asked after jotting down their beer order.

Rory looked at Dean and he merely shrugged. "We're going to need a minute."

"No problem." Maria smiled as she walked away.

"So, what kind of pizza do you want?" Rory asked, suddenly feeling like they were teenagers on their first date again.

"What ever you want is fine," Dean told her amiably.

"Seriously? You have no opinion on the pizza? Fine then I think we should get the Carnivore, it has every kind of meat you can imagine," she suggested, knowing he would not like a pizza that was covered in 5 kinds of meat.

"If that's what you want…"

"Okay, what's going on here? You hate overly meaty pizza."

"I just want you to be happy."

"Well just letting me have my way on things like this isn't the way to achieve that."

"Oh. Well then how about just Hawaiian?" he said after a moment, finally making a decision of some sort.

"Half Hawaiian half Carnivore?" she asked hopefully. The mere mention of the meaty deliciousness made her mouth water.

"I think that's a good compromise," he said with smile.

They were both silent for a minute until Maria came by to drop off the beer and the breadsticks. "Did you two decided what you wanted?" she asked as she set down the beer.

"Yep, half Carnivore, half Hawaiian. Tell Max the Carnivore is for me," Rory instructed.

"Will do."

"You know the chef too?" Dean asked.

"Yep. He'll make my carnivore extra meaty." She grinned excitedly.

"You are so having a heart attack before you're 30."

She shook her head dismissively. "Not a chance, my Gilmore constitution will hold out at least into my 40s. Look at my mom… she's 38 and hasn't had a problem yet."

"Right," Dean said sarcastically. "I wouldn't take the 'my mom is fine so I will be too' defense to the bank there."

Rory shot him a dirty look and set about eating her breadsticks and drinking beer, sitting in a relatively comfortable silence until the food arrived.

"Here ya go guys!" Maria said as she set down the pie. "Rory, Max added extra bacon and extra pepperoni for you."

"Perfect!" she exclaimed as she slid the first slice from the pan to her plate.

After the first slice was consumed Dean cleared his throat causing Rory to look up at him. "So, what are your plans after dinner?"

"Well, I've got to back to my office and grab my laptop, then I thought I'd head home. You?"

"You have to go back to work?"

"It's only to pick up something, it'll take 5 minutes, 10 tops," she said defensively.

"I was hoping we could watch a movie when you got home."

"We can! An extra few minutes isn't going to hurt anything."

"Maybe not for you, but I have to get up at 4:00 am to go to work," he said harshly.

She sighed deeply before responding to him. "Maybe we could just watch a couple episodes of Family Guy or something?"

"Whatever."

"Do you want to get the rest of this to go and head home now?" she asked.

"No," he said sullenly.

She rolled her eyes and grabbed another slice of pizza. "Do you want me to refill your beer?"

"No I'm good."

"Great," she replied shortly, plastering a fake smile on her face.

* * *

After spending the rest of dinner in silence Dean walked Rory back to her office.

"Are you coming home?" he asked quickly.

"Of course I'm coming home, when have I not come home?"

"I don't know."

"Look, go on home. I'm going to grab my laptop and add one little line to my article, then I'll be home."

"Okay," he said hesitantly. "I'll see you there."

She waved as he walked away, but he didn't wave back. When he turned the corner she keyed herself into her office, and went to retrieve her laptop.

She sat down harshly at her desk and put her head in her hands, silently wondering about What Might Have Been: how they got here instead of anywhere else, and if they'd ever get back to where they were once upon a time when they were happy.

* * *

**AN: I know it's a little harsh, but I really didn't like Dean the second time around. **

**Let me know what you think! **

**I don't own the song or the show. I completely made up Geno's and the Carnivore is an actual pizza, but at another restaurant. **

**Next up is Marty! (which will be much lighter)**

**S**


	6. Marty

"Tadah!" Rory shouted triumphantly as she walked into the living room holding a cardboard box.

"Tadah what?"

"I just unpacked the very last box."

"We've lived here for a month babe," Marty said with a smile.

"I know! It's only been a month!" Marty looked at her quizzically. "My mom and I moved into the Crap Shack when I was 11 and there are still boxes we haven't unpacked," she explained.

"Oh, well then I guess congratulations are in order." He tipped his head up from his spot on the couch so she could kiss him when she walked by on her way out the door to recycle the box.

She kissed him lightly and ran her hand across his shoulder. "I'm going to take this to the curb, is there any other garbage I should take out?"

"Rory Gilmore volunteering to take out the trash?" he teased. "I don't care if the bag is brand new in the kitchen… take it out anyway."

"Oh shush you!"

"But seriously, I think the bag in the kitchen is full, so would you take it?"

"Course," she said wandering into their kitchen to get the bag of trash, which was remarkably full. Especially considering they hardly ate at home. She walked back through the living room and Marty called out to her.

"I am taking you to dinner to celebrate this great feat. Tonight."

"Okay!" she said eagerly.

* * *

"You know," she started when she returned from the curb, "It's already 7:00, if we're going to dinner we should get a move on."

"Nah," Marty told her. "This is Chicago Rory. Restaurants take reservations until 10:00 at least, and nobody who's anybody eats before 8:00."

"How do you know?"

"Hello, I grew up here. Even if my family is working class, we still had the occasional meal out."

"But we've been out to eat at least 10 times in the month since we've been here," she said confused.

"But we haven't been out to a really nice restaurant yet."

"What about-"

"Compared to the place I'm taking you tonight, that one was a hole."

"You know where you're taking me?"

"Made reservations while you were taking the trash out. Can't let the only time my girl's ever fully unpacked go by unobserved now can I?"

"You're really sweet," she told him as she headed over to where he was sitting.

"Thanks," he replied, grabbing her hand and pulling her into his lap.

"So what time is our reservation?" she asked coyly, running one hand through his hair and the other down his arm.

"Not until 9:00."

"Perfect, then we have time." She leaned in and kissed him thoroughly, deftly unbuttoning his shirt as she went.

* * *

"Yes, Harrison party of two," Marty told the hostess when they arrived at the restaurant a mere minute before their reservation. "You almost made us late," he whispered in Rory's ear.

"You enjoyed every minute of it," she whispered back.

"Well of course." He smiled.

"Right this way please," the hostess said, grabbing a pair of menus and leading them to a high backed U shaped booth in the corner. "Will this do?"

"Perfect," Marty told her. He helped Rory out of her coat, and watched as she slid into the booth.

Rory picked up her menu and began to peruse the fine French cuisine. The food looked amazing, and pricy. "Marty, this place is so expensive! Can we afford it?" she asked. She had just started at the Chicago Sun Times, and Marty had just joined a firm as a junior accountant. Neither job paid particularly well. Well enough to pay the bills, and have a little left over, but not enough to be careless with money by any means.

Marty winked at her, "This is a celebration Rory. For the first time in your adult life you've been entirely unpacked!" He paused for a moment, then continued. "What are you having?"

"I think I'm going to have the ratatouille."

"Really? All I can think of when I hear that is rats in the kitchen," Marty told her with a laugh.

"I know, but I've been wanting to try it since I saw the movie."

"Okay then. And for starter?"

"I don't need one."

"You love appetizers! Of course you need one."

"I'd rather have dessert," she told him.

"Rory, tonight, for once, money is no object. I want you to have it all."

"All because I completely unpacked?"

"Yes!" he said with a mysterious smile.

"Fine, I'll have the cheese plate to start, and chocolate mousse for dessert. What are you having?"

"I thought I'd have the cassoulet, and crème brulee for dessert," he answered.

The waitress arrived at that moment to take their order, and in addition to all the food, Marty ordered a decent bottle of red wine to accompany it.

* * *

The wine and food were delicious, and Rory and Marty made easy conversation through out the meal. They talked about work, vacations they'd like to take, their friends at Yale, and pretty much any thing else under the sun.

When dessert was delivered, Rory noticed that Marty got suddenly quiet. "Marty are you okay? Is something wrong with your dessert?"

He cleared his throat, "No, the dessert is great, but I think the cassoulet upset my stomach, I'll be right back."

Rory set her spoon down, not wanting to finish her dessert while he was gone, and asked the waitress for a cup of coffee to accompany it. She pulled out her phone and decided to check her email while she waited.

Ten minutes later Marty returned looking decidedly better. "All better?" she asked.

"Uhm, yeah," he replied.

She picked up her spoon and went back to her mousse, and he picked up his spoon and went back to his crème brulee.

"Rory?" he asked a moment later.

"Yeah?"

"Uh… nevermind."

"Okay."

A few more minutes passed and Marty spoke again. "Rory?"

"Yeah?" Rory said slightly irritated.

"I… uh…" he stuttered.

"Just spit it out Marty," she said with a smile.

"Willyoumarryme?" he said in a rush.

"What?" she asked, not understanding him the first time.

"Will. You. Marry. Me," he said slower and more confidently. He pulled a small black box out of his pocket and presented it to her.

"Yes!" she said excited.

He smiled and sighed in relief, then opened the black velvet box to remove a brilliant round diamond affixed to a thin gold band. She held out her left hand, and he slid the diamond on her finger, then leaned in to kiss her, sealing the deal.

A minute later she broke the kiss. "So this dinner wasn't really to celebrate my finally unpacking all the way was it?"

He grinned at her, "nope."

"How long have you been planning this?"

"A while."

"What were you going to do if I didn't finish unpacking today?" she asked curiously.

"Make up some other reason to celebrate, I guess."

"I love you."

"I love you too."

* * *

**AN: Well, here's Marty. Let me know what you think!**

**I don't own the show or the song… and thanks again to Miguel51's Kismet for giving Marty a last name and a city to locate them in.**

**Up next – Logan I**

**S**


	7. Logan I

A soft shuffling sound woke Rory and she immediately looked at the clock, then to the other side of the bed to find it empty.

"Logan?" she called hoarsely.

"I'm here Ace."

"Why are you up at 4:00 am?" she asked.

"I've got to go to a meeting. Go back to sleep."

"Why are you having a meeting at 4 am?" She sat up in bed and rubbed her eyes.

"Video conference with the London office."

"Oh. I'm sorry I forgot." She yawned and laid back down in the bed.

"You didn't forget about it, I just found out about it 30 minutes ago."

"Mitchum couldn't give you 6 whole hours of notice?" she asked sarcastically.

"Apparently not. Go back to sleep Ace. I'll see you tonight."

"Kay," she yawned. "Love you."

"I love you too."

* * *

She woke again at 9:00 to the smell of brewing coffee. "Logan?" she called wondering if he had come home for some reason.

There was no answer. She slid out of bed and pulled her robe on before padding out to the kitchen. Logan must have set the timer on the coffee pot because it had just finished brewing a fresh pot. She poured herself a steaming mug and sat down at the counter to read the morning paper.

Before she was even half way through the first section her cell phone rang.

"Hello?" she answered when she finally dug it out of her purse.

"Rory?"

"Yes Grandma."

"I wanted to go over the final details for the DAR dinner tonight," her grandmother explained.

"We went over the details yesterday afternoon."

"I know, but-"

"Grandma, I've been planning DAR events for the last two years, I know how they work and what needs to be done. We don't need to go over every one a thousand times."

"Well if the event turns out poorly that reflects on me," Emily said sharply.

"Have any of my events ever turned out poorly?"

"That Russian Tea," Emily reminded her.

"That turned out poorly because you decided to yell at me in the middle of the event, not because of any planning on my part."

"Don't take that tone with me young lady."

"Grandma do you have a specific concern about the event? If so I'm happy to address it, but if not, then I'll see you there tonight."

"Do you have a plan for the unexpected guests that always seem to turn up?" Emily asked hoping to catch her off guard.

"Well the Huntzbergers already RSVP'd and they're usually the ones that turn up last minute, but yes I do. I have an extra table ready to be rolled out at a moments notice to be placed in the center of the room, so as to displace no one else."

"Well," Emily started with a huff, "I suppose you've got it all covered."

"I do. I'll see you tonight Grandma."

"Goodbye." The phone clicked off.

"Well goodbye to you too Grandma," Rory said to the severed connection. She sighed and grabbed a tablet from the corner to begin her to do list. She wrote To Do neatly at the top of the page, then stared at it trying to figure out where to start. She wondered how on Earth she got here instead of to What Might Have Been. Looking back, it seemed like one minute everything was perfect, and the next everything had turned to crap. She was supposed to be a foreign correspondent, not a trophy wife – well not wife, she and Logan weren't married, but trophy girlfriend.

The majority of the reason Logan's parents didn't like her was because she wanted to have her own career, she didn't have that now, and they still didn't like her. _Get new life _she wrote on the list, then added a bunch of things she actually needed to accomplish. She glanced up at the clock on the wall to see that it was almost 10, she needed to get in the shower before the phone calls from all the vendors started coming in, other wise she'd never get a shower. She took her last swallow of coffee and headed to the shower.

* * *

The event started at 8:00, and Rory needed to be there by 6:30 to start letting the staff in, so around 5:00 she began getting ready, blowing out her hair and putting it up just so. She was just slipping into her dress when she heard Logan arrive home right before 6:00.

"Ace?" he called.

"In the bedroom," she called back. She heard him drop his keys on the table by the door and set his briefcase down next to the couch, his footsteps growing louder as he neared.

"You look nice, what do you have going on tonight?"

"Logan!" she exclaimed, "the DAR dinner."

"That's tonight?" he asked.

"Yes that's tonight."

"Do I have to go?" he asked.

"Yes Logan you have to go. I put this on your calendar weeks ago."

"But I'm supposed to meet Colin and Finn for drinks, I just came home to change my clothes. I've been in this suit for 16 hours now and it's driving me crazy."

"You have to go to this dinner," she told him sharply.

"You know what, I am sick and tired of being told what I have to do. I get enough of it from my dad, I don't need it from you too," Logan shouted.

Rory just stared at him. "Well you know what, so am I," she finally shouted back. "But you can't always get what you want."

"Thank you Mick Jagger," he retorted snidely.

She shot him a death glare but he didn't budge.

"I'm having drinks with Colin and Finn."

"I have to go," she said slipping her feet into her matching Manolos. "How about a compromise?" she suggested as she walked toward the door.

"What'd you have in mind?"

"A quick drink with Colin and Finn before the dinner, and a promise to schedule less of these society things on the calendar in the future," she offered.

"How about a quick drink tonight, and a boys trip to Vegas in the near future," he countered.

"Only if I get a girls trip to LA," she countered back.

"Done," he said sticking out his hand to shake on it. She took his hand and shook it. "So what time do I need to be there?"

"8:00, in your tux," she called to him over her shoulder.

"My tux," he moaned.

"Sor-ry!" she called back.

* * *

The event went off without a hitch. There weren't even any last minute guests. Soon it was 11:00 and she was saying goodnight to people as they left.

"Rory, lovely party."

"Thanks Grandpa," she replied hugging Richard before he left.

"It turned out okay," Emily said from behind him.

"Well I know it's not nearly as good as one of your parties Grandma, but I'm getting there," she said placating her grandmother. She hugged her goodbye as well, and continued on to bid farewell to the next guest.

"Excuse," she heard Logan's voice from behind the couple she was saying goodbye to, "I'm sorry to interrupt, but may I have a quick word with my girlfriend?"

"Of course," the older woman said with a smile, blushing slightly when Logan winked at her.

"Hey Logan."

"Are you almost done here?" he asked.

"I've probably got another hour, I have to supervise the cleanup crew," she explained.

"Well I'm going to head home."

"Okay. I'll see you there," she said leaning in so he could kiss her cheek.

"I'll be waiting," he whispered in her ear.

* * *

By the time Rory unlocked the door to their apartment it was well after midnight. She really wanted to talk to Logan, but she figured after his early morning meeting, he'd be sound asleep. She pushed the door open, surprised to find the lights on and the smell of fresh brewed coffee filling the air.

"Logan?" She waited for a moment, but didn't get an answer. She toed off her shoes and walked into the living room to find Logan asleep on the couch with a steaming cup of coffee in front of him. "Logan," she said again more softly, as she reached out and gently shook his arm.

"Mmmm," he groaned. "Ace?"

"I'm home. I didn't want to wake you, but I know your back will be killing you tomorrow if you spend all night on this couch."

"S'okay," he mumbled. "I wanted to talk to you anyhow. Why don't you go get a cup of coffee?"

"Okay," she said leerily. She poured a steaming cup of the nectar of the gods into her favorite Yale mug and went to take a seat next to him on the couch. "So, what's on your mind Huntzberger?"

"You," he said simply.

"What about me?" she asked.

"You're not happy. I don't like it."

"What are you talking about Logan?"

"All you do is work at the DAR and plan functions for various charities, you're miserable."

"I am not," she retorted indignantly.

"Yes you are. You don't talk to Paris anymore, you don't talk to Lane, and you hardly speak to your mother."

"So what? People change they get new friends."

"Rory the ladies in the DAR aren't your friends!" Logan exclaimed. "You also don't read the newspaper with a red pen in hand anymore. Hell you hardly read the newspaper anymore. You're not the girl I used to know."

"Well you're not the guy I used to know either."

"What do you mean by that?"

"You kowtow to your father's every whim! You go along with him even when you disagree! And I do read the newspaper. Every day!" she said trying to defend herself.

"You used to want to do more than read the newspaper."

"Yeah, well, 'I don't have it'."

"My father was so wrong Ace, but by quitting school and not writing anymore, you're just proving him right. I hate it when my father is right."

"Then what do you want Logan? Do you want to break up?" she asked, her eyes filling with tears.

"No! I love you. And you and I, we're good. I just miss the old Rory."

"Sometimes I do to," she said quietly. "What can I do Logan?"

"Go back to school. Finish your degree, take the journalism world by storm, and prove my father wrong!"

"What if Yale won't let me come back?"

"They will."

"What about the old Logan?" she asked.

"He's going to make a comeback too. Now it's late, and we both have big days ahead of us tomorrow, so lets go to bed."

He stood up and extended his hand to her, she took it and he led her to the bedroom.

"Logan?" she started tentatively.

"Yeah?"

"Thanks."

"Anytime."

* * *

**AN: This one was hard to write. I love Logan and I'm a huge Rogan fan, but I honestly had a hard time figuring out where Rory would be if she and Logan never broke up the first time. That seemed to be the catalyst that got her back into Yale and back on good terms with her mom. **

**Anyhow – I don't own any of it. Please review and let me know what you think.**

**Next up: Jess II**

**S**


	8. Jess II

**Author's Note:**

**To address a couple of reviews: First, I am aware that Rory and Dean were together 3 times, not just two, but I felt that the first two times they were together, the characters were substantially the same. Thus had Rory stayed with Dean the first time or the second time, What Might Have Been would likely have been the exact same place. **

**Thus since she and Tristan were never actually together, I have his bit set after Dean the first time, but before Jess. **

**As to Jess, because his return in season 4 was for two minutes just asking her to go away with him, it does not get it's own chapter. (Also, I have no idea how Jess changed between leaving for California and coming to see Rory at Yale) Jess II is written as if Jess and Rory got together in Season 6.**

* * *

Rory Gilmore stood in front of her full-length mirror, applying her lipstick, and getting ready to go on yet another interview.

"Jess, have you seen my Birkin Bag?"

"Your what bag?" he asked.

"My Birkin Bag, it's my hot pink shoulder bag," she explained.

"I can't believe you name your bags," he said with a sigh, "but I think it's on the couch."

"I didn't name the bag, that's just the brand of the bag."

Jess rolled his eyes, "I can't believe you've become one of those people."

"What people?" she asked.

"Those 'my Coach sunglasses don't match my Fendi purse,' people," he explained in a faked posh voice.

"People with a sense of style?"

"No! The overly label conscious."

"Right," she said with a snort. "Can you find my other Christian Louboutin shoe?" She added fuel to his fire and held up a high heel.

Jess shot her a dark look.

"Please? I'm in a hurry." She bent down and began to dig for the shoe in the hall closet.

"Alright I'll check the bedroom," he said. A minute later he called out to her "I found it!"

"Thank you!" she exclaimed. "Where was it?"

"Next to your Old Navy flip flop," he told her with a smile as he handed her the shoe. He kissed her cheek.

"I wonder how my shoes got separated," she said absently.

"I don't know, but I think we need to get a bigger place." Jess had moved into a one bedroom apartment when he and Rory got back together. Living with 3 other guys was not conducive to weekend visits from his girlfriend. After she graduated she moved in with him in Philadelphia and she'd looking for a job ever since, and the two of them had been cramped in a tiny one bedroom apartment.

"As soon as I get a job," she agreed.

"Have fun stormin' the castle," he told her. It had become their way of tell each other good luck without the jinx of actually saying the words.

"You too," she said knowing he had two potential client meetings at Truncheon. She slipped on her heels, grabbed her Birkin bag and walked out the door.

* * *

The Philadelphia Inquirer was the fifth major paper that Rory had interviewed with. She'd resolutely avoided any of the Huntzberger-owned papers, but if she didn't get this job she might be forced to apply at one.

She walked into the lobby of the paper projecting an air of confidence that she didn't actually feel. "Yes, Rory Gilmore to see Tom Spaulding," she told the receptionist.

"Go ahead and have a seat Ms. Gilmore, Mr. Spaulding is just finishing up a meeting and will be with you in a moment."

Rory nodded in understanding and took a seat in one of hard leather chairs nearest the editor's door. She pulled out her portfolio, flipping through it one last time, and then made a few notes about questions to ask during the interview process. She heard the door open next to her and finished writing her sentence before she looked up.

"Rory?" She heard a familiar voice, but she couldn't quite place it.

"Yes?" she said in return finally looking up into the eyes of Mitchum Huntzberger. "Mitchum, hi."

"What are you doing here?" he asked.

Rory noticed he was standing next to a man that was in all likelihood the editor she was about to interview with. "I'm here for an interview," she told him as politely as possible. She really wanted to ask him why it mattered, but didn't want to appear rude to him in front of this editor. "What are you doing here?"

"Just checking things out," he answered vaguely. He turned to the man standing next to him, "Well I'd better get going Tom, I'll call you back later in the week, and maybe we can work out some details." The man nodded. "Rory, it was nice to see you. Give my regards to Richard and Emily."

She tried not to look incredulous as she nodded at his request. "Give my regards to your family as well." She glanced over at Tom and watched his face as Mitchum walked away. She swore she could smell sulfur, but knew better than to ask him if he could smell it as well.

It took a minute or so for Tom to pull himself back together and remember that Rory was there. While Rory waited patiently she thought about What Might Have Been, had she and Logan stayed together she'd likely already have a job, with no one wanting to upset the Huntzberger heir and all, but she knew she'd rather do it on her own, even if she was so tired of interviewing the mere thought of it made her head hurt.

"I'm sorry," Tom said suddenly. "Are you Ms. Gilmore?"

"Yes. Hi. Rory Gilmore. It's a pleasure to meet you," she said as she stuck out her hand to shake his.

"Come on into my office," he told her when he dropped her hand. He turned and walked towards the office with her following close on his heels. "So, how do you know Mitchum Huntzberger?"

"Wow, you really cut right to the chase don't you," Rory said flippantly, taken a little aback at the blunt question. She waited a beat for him to explain or withdraw the question, but he just continued to stare at her. "I went to Yale, and I interned at the Stamford Eagle Gazette with him." She hoped that answer was satisfactory, she really didn't want to talk about Logan right now.

"Oh. And you know his family?" Tom asked.

"Yes, but I'm not sure how that's relevant," she responded.

Tom shook his head as though he were clearing away dusty thoughts. "You're right it's not at all relevant. Why don't you have a seat, while I look through your portfolio again," he said.

"Thank you," she replied taking a seat across from his desk, and watching with interest as he flipped through her portfolio. He smiled occasionally as he read something that interested him, and she curiously wondered which article it was.

"You have a very impressive portfolio Ms. Gilmore. So what brings you down to Philadelphia?"

"My boyfriend," she said politely. "He's one of the owners of a small independent publishing house," she paused for a moment trying to determine whether to continue. Tom smiled encouragingly and she pressed on, "Truncheon Books."

"Why do you think you'd be an asset to the Inquirer?"

"I have a lot of experience writing… is Huntzberger Publishing Group interested in acquiring the Inquirer?" she asked out of nowhere. She knew it wasn't any of her business, but she couldn't help but ask just the same.

"Well…" Tom started slowly, likely weighing exactly what he should or could say. "I honestly don't know. Does that matter to you?"

She shrugged, trying to determine if it really did matter to her. "I guess not. I think I'd just like to know in advance if I would be working with Mitchum again."

"Well you seem to be in a better place to know that than I do," Tom told her. She looked at him curiously, obviously confused by his statement. "Well you are on a first name basis with him."

Again she shrugged, then redirected the conversation to where it was before she interrupted herself. "As I was saying, I've written a lot, I was a staff writer for the Yale Daily News for 2 years before I became the editor in chief. I also did some writing for the Stamford Eagle Gazette."

"What kind of writing are you looking to do here?" he asked.

"I really like to do all of it. Features, news, reviews, heck once I even wrote a piece on the repaving of a parking lot," she explained with a smile.

"Do you have a problem traveling?"

"No, in fact, I quite enjoy it."

"Do you have any questions for me?"

"Do you know when you expect to make a decision on the position?" she asked, surprised at her own forwardness.

"I have a few more candidates to interview, and I intend to have a decision made by the end of the week."

"Okay."

"Anything else?" he asked.

"I don't think so, thank you," she replied.

"It was a pleasure meeting you Ms. Gilmore, I'm sure I'll be speaking to you in the near future." He stood up, smiled at her and extended his hand for her to shake it.

She stood up and shook his hand, "thank you for your time Mr. Spaulding."

* * *

Her drive back to their apartment took an inordinate amount of time, thanks to a traffic accident that blocked three lanes of the road, and by the time she got home she had convinced herself that she'd never get the job at the Inquirer and it was all Mitchum's fault.

She let herself into the apartment and headed straight for the freezer. The only thing that could make her day better right now was a carton of Phish Food and great news from Jess about his day.

She was on the couch about two-thirds of the way through the carton when she heard the key click in the lock. "Hey babe," she called to him.

"Hey," he replied sullenly. "How did the interview go?"

"Nope. You first. How did your client interviews go?" She fervently hoped for good news, she needed something to celebrate.

He grabbed her Birkin Bag off the couch and threw it across the room angrily, then plopped down on the couch next to her. "Not good."

"I'm sorry, but that doesn't mean you need to throw ten thousand dollars worth of handbag across the room."

He looked at her incredulously, then at the handbag, then back at her. "Why the hell do you have a $10,000.00 purse?"

"It was a gift," she told him.

"That **thing **could pay our rent for 6 months!" he yelled.

"Why are you yelling? It's not like I paid ten grand for the bag."

"I can't afford to buy you a bag like that," he said weakly.

"So what? I didn't ask you to buy me a bag like that. Hell I didn't ask for this bag in the first place."

He nodded, accepting her answer for the moment. "So how was your interview?"

"Ran into Mitchum Huntzberger," she told him nonchalantly, not wanting to keep it from him, but not wanting him to overreact either.

Jess shoved his hands through his hair and sighed deeply. "Who are you?"

"Jess," she started nervously, "what are you talking about?"

"You wear designer shoes, carry a $10,000 purse and are on a first name basis with one of the worlds largest newspaper moguls."

"I'm still Rory. I can't change my past. You know that. You can't change yours either."

"I can't give you that life."

"I didn't ask you for it."

Jess stood up and began to pace the living room. Rory watched as he walked, wondering what his next move would be. He finally walked over to the door and grabbed his jacket.

"Jess, where are you going?" she asked.

"I need to think." He stormed out the door, slamming it behind him, and Rory began to think too.

* * *

**AN: Alright, all the things I don't own: Gilmore Girls, Coach, Fendi, Christian Louboutin shoes, a Birkin Bag, The Princess Bride, or Ben and Jerry's. **

**Thoughts behind this bit: I think that Rory, post Logan the first time, learned a bit about how the other side lives. And while I don't think she'd become a total snob, I think that she probably learned to appreciate a few of the finer things in life. **

**Let me know what you think! **

**Up Next: Logan II**

**Then an epilogue as per requested… I just don't know how it'll turn out yet. **

**So I guess a poll: If Rory got back together with any of her exes – post season 7 – who would you like to see, and why?**

**Please read and review - S**


	9. Logan II

"Logan, are you home?" Rory called as she entered the kitchen in their Palo Alto house.

"Out here Ace," he called.

She stuck her head out the sliding glass door to find Logan on the back porch, wearing an apron, holding very large tongs in one hand and a beer in the other. "How was your day?" she asked.

"My day was great. We've gotten a little more funding for the company, and Honor called to tell me she and Josh are expecting!"

"That's great! So why aren't we going out to celebrate?" Usually they went out to celebrate everything.

"I just felt like barbequing," he told her.

"My little chef," she commented with a smile.

"So how was your day Ace?"

"It was," she paused, trying to think of an appropriately descriptive word, "awkward."

"Why was your day awkward?" he asked, his voice full of concern.

"It's nothing really," she said dismissively. "I'm going to go change my clothes, I'll be back in a minute."

"Ace, is everything okay?"

"Yeah. I'll tell you all about it I promise, but I want to get out of this suit."

"Okay." He took another drink of his beer, then set it down to lift the lid on the barbeque and flip the chicken.

* * *

Rory slipped her shoes off and unzipped her skirt. She re-hung the skirt and jacket, and grabbed a pair of shorts and a tank top from the closet. She pulled her hair up into a ponytail then padded barefoot back outside.

"Much better," she announced when she arrived, wandering over to where Logan was standing to kiss him hello properly.

"I agree," he said a minute later, breaking the kiss to tend to dinner. "So why was your day so awkward?"

"Someone at the Chronicle let it slip that we're engaged," she told him.

"So what," he knew she wasn't keeping the engagement a secret. "I thought every one knew anyhow."

"They knew I was engaged, they just didn't know to whom."

"Are you ashamed of me Ace?" he asked mockingly.

"Never!" she exclaimed. "I just didn't want special treatment for being engaged to a Huntzberger."

"I guess I can see that. So who let it slip?" he asked.

"The editor I interviewed with. Apparently she called Mitchum as a reference check,"

Logan cut her off. "Wait, you put my dad on your references?"

"No!" she stated immediately. "Well not really. But he was my boss at the Stamford Eagle Gazette the first time. There are several other people in front of him, but I guess she couldn't resist a chance to talk to The Great Mitchum Huntzberger."

"So my dad told her we were engaged?" Logan asked confused.

"I guess," Rory told him with a shrug. "She didn't say anything at first, but today something came up about the troubles at The Globe, and she suggested that since I was practically related to Mitchum Huntzberger that I should call and interview him."

"Like my dad would give an interview about one of his tiny papers," Logan said with a laugh.

"I know, right?"

"So what did you tell her?"

"Well first I had to wait about 10 minutes for all of the chatter to die down, and then explain to everyone that while yes I am engaged to you, I'm not actually on great terms with Mitchum, and thus me interviewing him would be a Very Bad Idea."

"You didn't tell her that anyone trying to interview him would be a waste of time?" Logan asked.

"Nope. Might as well let her spin her wheels for a while."

"Wow, that's spiteful of you Ace," Logan said proudly.

"The rest of the day everyone was oddly quiet around me. Like I was a spy for the enemy camp or something," she said quietly.

Logan wrapped his arm around her. "I'm sorry Rory. Can I do anything to help you fix it?"

"No," she said wistfully, "adding more Huntzbergers into the fray will just make things worse. I've just got to ride it out."

"Okay. Well let me know…" She nodded. "Do you want to make some fresh guacamole from our avocado tree?"

"I can do that." She headed towards the tree in the middle of the back yard, and began to look for the ripest avocados.

* * *

Thirty minutes later they were sitting on their back deck eating corn chips and guacamole, barbequed chicken and corn on the cob. "You know what would make this perfect?" Rory asked.

"Bacon?" Logan supplied randomly.

"No… well maybe… but I was thinking a margarita."

"I think that could be managed," he said with a smile, standing from his seat to go make her a margarita. "Blended or on the rocks?"

"On the rocks is fine, it's quicker."

He returned a quick two minutes later placing a very large margarita in front of her. "Try that and let me know if it's strong enough."

She took a sip and inhaled sharply making a tight face. "Is there anything but tequila in here Logan?"

"Yes," he said defensively, "just not a lot of anything else."

* * *

They spent the next hour and a half enjoying their dinner, each others company, and the lingering sun in their back yard.

"I think with just a few more investors Paul, Bobbi and I will be able to actually start drawing paychecks," Logan told Rory excitedly.

The margarita made her nice and relaxed and she smiled at him. "I love you my little Work Dork."

"Well I'm glad to hear that, because there's something I need to tell you."

"What's that?" she asked smoothly, grateful for the alcohol that was coursing through her veins making it impossible for her to get to an overly tense and worried stage.

"My mother called today. She's put a hold on a Plaza in September."

"But Logan, we JUST got engaged," she emphasized.

"I know Ace, and I told her that," he explained calmly, "She just doesn't listen."

"I'll make her listen," Rory snarled angrily.

"Good luck with that Ace," Logan said with a smile. "And your grandmother called, something about having the shower in the Rose Room."

Rory smacked her forehead with her hand, again grateful for the alcohol, this time dulling her pain. "If we do this, the way they want it done, will they leave us alone after that?" she asked hopefully.

"I doubt it," he responded honestly. She looked up at him, and he could see the tears of frustration forming in her eyes. He reached out and took her hand, then slid his chair close to hers. "Rory, Ace, I am behind you one hundred percent. If you want to give this one to the families, I'll support that. If you want to tell them to screw themselves and elope to Vegas, I'll support that too. Hell, I'll support anything you want as long as it eventually ends up with us married and living happily ever after. Okay?"

She nodded and tightened her grip on his hand. "Thanks Logan."

"Anytime. You stay here and I'll go grab dessert."

While he went to retrieve dessert, she thought about her options. Her mom wasn't thrilled with the fact that she was marrying Logan, and having the wedding in two months would make matters worse, but her grandmother never got to throw Lorelai the society wedding she always wanted to, and the Plaza and the Rose Room may go a ways in healing that wound. She wanted to be engaged longer than two months, and she knew Shira would probably still hate her, even if Rory went along the wedding exactly as Shira wanted. She thought about eloping to Vegas, with Colin, Finn, Stephanie, Honor, Lane and Paris… and probably Lorelai. She thought about her old dream, the town square in Stars Hollow.

"Ace, are you alright there?" Logan asked bringing her out of her thoughts and placing a large wedge of cake in front of her.

"Yep. Just thinking over our options," she told him.

"And?"

"We can't please everyone."

"I know."

"How would you feel about eloping to Vegas?" she asked with a saucy smile.

"You jump I jump Jack."

* * *

**AN: I don't own the show. I wish I did, then I'd be rich. **

**Up next – the epilogue… send me your ideas as to who she should end up with… (As a note… I'm not good at new characters… so it will be one of these guys)**

**Please read and review! **

**S**


	10. Epilogue

"Gilmore, wake up!" She was jostled awake by one of the other reporters on the bus.

"Huh?" she mumbled, momentarily confused.

"We're at the hotel. Time to get off the bus and resume your nap in your room."

"Uh thanks," she said politely. She shook her head to clear her thoughts, and began gathering her belongings.

* * *

Twenty minutes later she settled into her hotel room. As luck would have it, she drew the long straw and got the one single room. This would be the first night she'd spent completely alone since she joined the campaign.

She plopped down on her bed and fished out her iPod. After all the possibilities she'd run through during the last few days, she decided she needed to hear the song again.

_We could sit and talk about this all night long_

_And wonder why we didn't last_

_Yes they might be the best days_

_We will ever know_

_But we'll have to leave them in the past_

_So try not to think about_

_What might have been_

_'Cause that was then_

_And we have taken different roads_

_We can't go back again_

_There's no use giving in_

_And there's no way to know_

_What might have been_

The song was probably right, things were probably best left in the past. She grabbed her cell phone off the nightstand and began to dial.

"Loin fruit!" Lorelai answered cheerfully.

"I hate you!" Rory exclaimed.

"Hate_ moi_? You cannot hate the life giver – it's in the Gilmore Girls contract!" Lorelai responded, not taking her daughters hatred seriously.

"I don't think any court of law would uphold a contract signed by an infant."

"What's with the hatred kid?" Lorelai asked seriously.

"You put that stupid song on my iPod," Rory spat bitterly.

"Ha! Have you been singing Da Da Da all day long and pissing off your bus mates?"

"No. You put that song on there too?"

"If not Da Da Da, what are you talking about?"

"What Might Have Been."

"But that's a good song! It's one of the first country crossover ballads," Lorelai explained.

"Yeah, well, it's made me spend the majority of my last several days considering how my life might have turned out."

Lorelai chuckled softly. "I'm sorry kid. I honestly didn't think of that when I added it to your iPod."

"Well thanks a lot."

"Did you find any possible life you might like better?" her mother asked.

"Maybe."

"And?"

"Just maybe."

"You're not going to tell Mommy?" Lorelai whined.

"Not until I tell him."

"But then you'll tell me?"

"If it works. If it doesn't work… well, there will be payback," Rory said maliciously, well as maliciously as she could ever get when it came to her mother.

"Good luck Kid."

"Thanks Mom. I love you."

"Love you too Sweets."

She hung up the phone with her mother and began staring at the ceiling, hoping that it would give her the answers she'd been looking for, or if not the answers, the courage to make the call.

* * *

She poured herself a gigantic cup of coffee, with a shot of Baileys – if ever there was a time for an Irish Coffee now was it – and sat down nervously in the arm chair in her hotel room. She picked up her phone, and dialed a number she knew by heart, hoping that he hadn't changed his number.

"Hello?" he answered leerily on the second ring.

"Hey," she said quietly, "It's me."

"Hey," he responded. He didn't ask how she was or why she called. She nervously let the silence carry on for over a minute before he finally spoke again. "Rory, what's going on? Are you okay?"

"Uhm, yeah. Well actually, no, not really."

"Ohhhkay," he drawled.

"I'm in town."

"In my town?" he asked.

"Yeah. And I was wondering, do you want to meet up? Coffee or something?"

"Rory, I don't know…" he said hesitantly. She took a big sip of her coffee, feeling the alcohol burn as it made it's way down her throat.

"Please," she asked softly just shy of begging. "I made a mistake. You of all people should know how easy it is to make a mistake."

"Rory," he started warily. She waited for him to turn her down cold, thinking that right now anything would be better than this feeling of anticipation. "Fine. How about the Starbucks on 7th Downtown, tomorrow night at 8:00."

She thought about it for a moment, just to make sure her schedule would allow it. "That's perfect. Thanks Logan, I'll see you tomorrow."

She hung up her phone and took another large sip of her coffee. She didn't know how things would turn out tomorrow, but for now, she was happier than she'd been in a long time.

* * *

**AN: There you have it. The overwhelming majority wanted a reunion with Logan. **

**I hope you've enjoyed my story. I appreciate all of your reviews and feedback. Now, I promise, I'm going to get back to work on Winning Back The Gilmore Girls. Hopefully I'll get another chapter to you this week.**

**Thank you all for reading and reviewing!**

**S**


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